


One Night At Rhonda's

by JackTrades



Category: Supernatural
Genre: Dean in Panties, F/M, Feminization, PWP, Panties, Pegging
Language: English
Status: Completed
Published: 2016-01-23
Updated: 2016-01-23
Packaged: 2018-05-15 20:10:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,627
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5798332
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>Dean and Rhonda have sex.</p>
            </blockquote>





	One Night At Rhonda's

**Author's Note:**

> This work refers to slow jazz music at some point. If you would like a reference, I was listening to [Chet Baker ](https://youtu.be/H6mfWun73vI).

"You want me to what?" Oh boy, Dean knows he fucked up. Rhonda is royally pissed at him. Now he has a very hot, blonde woman looking like she's definitely kicking him out of bed.

Dean immediately gets flustered and attempts to backtrack, "Just talk to him. I mean, I have learned a lot from you. Like a lot lot. And he asked me what he should do with girls and I thought it would be more educational for him talking to a woman. He's so nerdy he'll probably have a lot of ques-"

Rhonda interrupts, "Let me get this straight: you want me to talk to your 15 year old brother about sex."

Dean isn't sure what the issue is, "Yeah?"

She eyes him for a moment before it dawns on her that, no, he does not understand why she's upset about this. "Dean, I'm almost ten years older than him. I'm pretty sure I could get arrested for that."

"You can't get arrested for talking!" Or could you?

The argument ensues, negotiation tactics kicked in, and suddenly a lifetime of lying and conning people works out to his advantage. Clothes aren't being put back on so he has a chance. He just needs to give her an incentive. "Look, you do this for me and I'll do something for you," he tries his damnedest to sound smooth and confident.

"Oh honey, you can't handle what I really want," she isn't trying, she actually is smooth and confident. Of course he takes the bait.

He grins with that smile that was part curious, part seductive, and completely naughty. "Try me," he crosses his arms in challenge.

"I wanna fuck you senseless," she always is blunt with him. Argument sex is a nice bonus in this situation.

"Oh hell yes," he is already making a move towards her when she stiff-arms him.

"I don't think that you are understanding: I. Fuck. You." She gives him a sly smile and waits for the gears to click into place.

In his defense, his entire relationship with her is based on mind blowing sex. He doesn't have too much blood flow to his brain. His innocence is on full display when he realizes what she was getting at. When he goes from confused to realization, he immediately blushes like the vanilla boy that she knows he is. Part of his appeal to her is the thrill of corrupting him. He might have kinky fantasies but he has certainly never acted on them before Rhonda. His freckles stood out more with the blush and wide eyes.

"Awwww, don’t be scared." She belittles him a little, he weirdly gets off on it, "It's okay if you don't want -"

"Who says I'm scared and don't want to?!" His reactions really are an open book to her.

"So you'd let me fuck you like a good little girl, just to help your brother out?"

"YES!"

"Bullshit," she starts fishing around on the floor and smiles, triumphant, when she finds her panties. "Prove it, call it a sign of good faith. You put these on and dance for me."

He considers it. "I do that and you'll help Sammy with his questions?" She nods. And just like that he pops up from the bed and grabs the panties from her as he stands.

She loves how eager he always is. Especially if it is even slightly taboo - he is willing to try anything once. He is rushing though. "Slow down, Speedy," she runs her fingers down his arm to his hand, "put them on nice and slow. I want to watch your reaction to it."

He listens. He takes a deep breath and bends to the floor stepping one foot into the leg hole of the satin panties, then the other, holding them around the middle of his calves as he looks up at her. "Slow," she purrs at him.

He goes achingly slow, letting them creep up inch by inch. The drag against the fine hair on his legs and the scrutiny of Rhonda are combining to make him really hard, really fast. He is already at half mast when he finally crept up to the top half of his thighs and could suddenly feel the waistband tickling against the back of his balls.

He decides to be cheeky about it and turns so she could watch him pull them over his ass. She is always complimenting him on it. He expects to like her reaction to it, she is ordering him around and he is just taking it; he is not expecting his reaction to it though. The material clinging to him should have been uncomfortable, but it isn't. He pulls them up with his cock sticking out the top with the elastic half holding it to his smooth stomach.

She pipes up making a tisking sound, "Tuck it in."

Dean huffs and awkwardly shuffles his hand in the panties, trying to figure out how to contain himself. Rhonda thankfully contains her laugh. She finds his need to please adorable and endearing. He finally gets himself together and snaps the elastic low along his stomach. His erection tents the front and pulls the panties away from his thighs. His balls are pressed impossibly close to his body.

Rhonda grins, "How's it feel?"

Dean blushes more, now down his chest. He worries his lip before answering, "Feels good."

Rhonda shimmies to the edge of the bed close to him. She cups him through the material, "Yeah? You gonna be a good girl and wear these from now on?" Dean can't contain his moan. He's a sucker for dirty talk. It only encourages her, "Or... are you going to be a naughty girl and wear a frilly thong?" Dean is leaking precome onto the satin material forming a wet spot in the front of the panties. She slaps his ass when he doesn't respond. "Answer me!"

Dean gasps at the stinging blow. "These." She smirks and he adds, "I like being a good girl for you."

"Yeah, I bet you do." She leans over to her laptop on the nightstand and plays slow jazz music. He looks confused again. She purrs, "I said put those on and dance for me, sweetheart."

Dean isn't out of his element here. The panties are a new thing but the dancing is something he has experience in. He sways back and forth to the music while trailing a hand down his chest and over his crotch. He hooks his thumbs into the waistband and tugs without actually revealing anything then pushes her back. He straddles her, gyrating in small circles while he wraps his arms around her neck.

She never really lets him get the upper hand. She tugs the hem of the panties between his cheeks and digs her fingers into the meaty part of his butt. His breath hitches and his movements falter. He tries to cover his surprise by pulling her into a sloppy kiss as he resumes his gyrations. She takes the opportunity to slide a hand into the fabric and run a finger over his hole. He stiffens and pulls away. She rubs gently between his shoulders, "Just trust me. You'll like it."

Dean can't help it. He wants to try everything and if she says he'll like it, she doesn't have a reason to lead him astray. He bites his lip and nods to let her know it's okay to continue.

She pushes two fingers to his mouth and he instinctually sucks them hard as he swirls his tongue around them. She pulls them out of his mouth and distracts him with a sloppy kiss. As he melts into her, she slides a hand down the top of the panties and circles his hole again. She breaks the kiss and leans back, "You ever do this before?"

Dean looks away, "No."

She runs her free hand through his hair, "Not even by yourself?"

He hesitates as if it's an odd question, "... no."

"Not with another guy?"

"No," he sees her quirk an eyebrow and volunteers more information. "Only ever did kissing and hand jobs with another guy."

She smiles, "Luckily for you, I have done this before. Don't worry, I'll make it good for you." She taps his hip. "Get up." Dean slides off the bed and stands next to it awaiting her next instruction. She looks him over before standing next to him and stroking his shoulders. "You want to do this, right? I don't want to pressure you if you are not into it."

Dean shrugs, "I never did it before. Not gonna know if I like it or not unless I try..."

"It's not for everyone."

Dean gives her a shy smile, "I want to try it. I trust you."

She snaps the elastic of the panties against his hip. "Okay, take these off and get on the bed. Hands and knees, and make sure that cute butt of yours is nice and high."

She crotches down and opens the bottom drawer of her nightstand. She tosses a bottle of lubricant on the bed and digs around in the drawer. She eventually produces a small butt plug and what Dean assumes is a strap-on. He scrunches his face, "All of this is necessary?"

She laughs lightheartedly, "Not necessary, but I need to lube you up before for sure. I'm going to use this," she picks up the plug, "First. It'll give you an idea of if you like it or not." She holds up the other contraption. The business end of it is as pink as the panties he just took off. "I have to put this on if I'm going to peg you."

"Peg?" Dean is snickering at the word.

"Hey, I didn't make up the term. Give me a minute, this is a little complicated to get on." She steps into the harness and pulls it up. There's part of it that slides inside of her. She puts some lube on it before pushing it in. Dean bites back a moan watching that. She adjusts and tightens it until she's comfortable. Dean is scoping out the dildo portion and is relieved to see it isn't monster-sized. It's only about five inches long and on the thinner side. She catches him, "I have a bigger one but I want to be gentle since you are getting your cherry popped."

Dean flashes a cocky grin, "I can take it!"

She rolls her eyes, "We'll revisit it after you take this one..." She gets on the bed and settles behind him with the bottle of lube in her hand. She pops the cap and pours some on her fingers. "I'm going to touch you now." She tosses the lube on the bed for now and rubs his lower back. She tentatively circles around his hole a few times; he squirms from the weird sensation but doesn't protest. She pushes one finger in to the first knuckle, "Dean, you have to breathe. Try to relax."

Dean lets out a long sigh and laughs, "Sorry. Didn't realize I was doing that." He takes a few deep breaths as she pumps her finger in and out at a slow pace. When she adds a second finger, he squirms again. "Feels weird."

She pumps and starts spreading them apart slightly. "Weird like bad?"

"Not bad but it feels strange like - Hnnnnghhhh," Dean drops his head and pushes back unconsciously. "Holy shit! Do that again!"

Rhonda crooks her fingers and brushes over his prostate again. "Easy." She continues her movements, occasionally brushing over that spot to get another one of those high-pitched noises out of him. He practically whined when she withdrew her fingers. "I'm going to use this on you now." She held up the plug in his line of sight.

"Okay," he huffs out.

She applies a generous amount of lube to the toy. It is about as wide as three of her fingers at its largest point. She eases it in and gently pushes it in. "You still good?"

Dean nods, "Still feels weird..."

"This is just to stretch you out. I'll make sure it feels good when I've got this in you," she strokes her cock for emphasis. She pumps the toy in and out, not pushing past the widest point, as she drizzles lube on the strap-on. When she is confident that Dean is sufficiently prepped, she withdraws the toy and places a quick kiss on his shoulder blade. "Flip over. I want to see your pretty face while I fuck you."

Dean scrambles to comply, nearly tangling himself in the sheets in the process. He is flat on his back with his legs stretched out. "How should I..."

Rhonda knows what he is getting at. She climbs between his legs and gently pushes behind his knees. She guides his knees up towards his chest. Grabbing a pillow, she shoves it under his back to make him more comfortable. She grips the base of her cock and guides it to his hole. When she starts to push in, she looks at his face. She loves the wide-eyed fascination he has every time he tries something new. She keeps pushing until she's buried to the hilt and leans over him to kiss his neck and chest. She ghosts up to his ear, "Just let me know when you're okay with me moving?"

Dean takes several deep breaths again. He thought it was small but he feels so full. It doesn't hurt or feel bad, but it doesn't feel good either. He can feel himself getting hard again from Rhonda's other movements. He finally nods, "Rhonda?"

She pulls back so she can see him better, "Yeah?"

He blushes again, "Are you gonna be gentle or rough with me?"

She gives him a chaste kiss on the lips. "How do you want it?"

He thinks before answering. "Rough."

She raises an eyebrow, "You're going to be sore tomorrow if I'm rough."

Dean cracks a filthy smile, "Good."

She knew just how to wipe that look off his face. She pulled out, biting back her own moan as the drag jostled the part inside her, then snapped her hips forward. Dean let out a small moan. She repeats the action a few more times before readjusting their position. She leans back on her knees. "Put your legs on my shoulders."

She lifts his hips slightly and snaps forward again. The change in angle did wonders for Dean. He moans loudly then shoves his fist to his own mouth trying to quiet himself. Rhonda keeps pace, her hips slap against the backs of his thighs and Dean is certain that he'll have bruises.

She let go of his hip with one hand and begins jerking his erection at the same pace. Dean finally breaks from that. He lets loose an intangible string of 'please,' 'yes,' and something resembling her name before he is coming. His chest and stomach are covered as she fucks him through it.

She gingerly pulls out of him and lowers his legs to the bed. She takes a moment to admire what a spent mess he looks like. A naughty thought occurs to her and she decides to act. She slicks the plug again and shoves it into him. Dean grunts in discomfort. She grabs the panties from the floor and tosses them at Dean, "Put those on under your jeans. You're going to wear them while I talk to your brother. Then I am going to fuck you again when you bring me back here."

Dean isn't sure how long they will be in this town. All he knows for sure is that he is never going to forget Rhonda Hurley.

**Author's Note:**

> Friendly reminder that pre-series, 19 year old Dean would look like this:  
>   
> Aaaaaand young, in series Dean:  
> 
> 
> Sources:  
> http://thevioletprincess.tumblr.com/post/137053783257/okay  
> http://dean-senpai.tumblr.com/post/114369218644
> 
> Comments and kudos are greatly appreciated!


End file.
